Blog•Oct 16, 2025
20VC X SaaStr Is Back!! The New Rules of Venture: Portfolio Construction, Kingmaking, and When Founders Walk Away
Venture investing is being rewritten as AI startups compress time-to-unicorns and force a rethinking of portfolio construction: early-stage funds now need ~20–25 initial bets before concentrating ~75% of capital into 3–5 winners, while the exit threshold has risen from ~$200M to ~$400M ARR, extending time to liquidity by 2–3 years. Recent deals—Goldman’s $665M purchase of Industry Ventures (≈10% of its $7B AUM) and founders taking $3.5B-plus offers—underscore shifting economics, secondary-market valuations, and founder liquidity that can short-circuit multi-period investor dynamics. The result: managers must redesign follow-on allocation, enforce stronger founder protections (vesting/repurchase rights), and weigh massive compute/token capital needs against uncertain long-term returns as AI scales. These trends recalibrate risk, ownership concentration, and exit planning across the venture ecosystem.
By SaaStr
Blog•Oct 16, 2025
In Startups, The Harder You Work in Sales, The More Good Leads You Get
Jason Lemkin argues that in startups the highest-quality leads concentrate with the hardest-working, most prepared sales reps, creating a self-reinforcing “hustle feedback loop.” He cites internal data showing top-quartile activity reps closed deals at 2.3x the rate, had 31% larger...
By SaaStr
Blog•Oct 15, 2025
5 Critical Phases of Building Your SaaS Sales Machine: Jason Lemkin + Harry Stebbings
SaaStr co-founder Jason Lemkin and investor/podcaster Harry Stebbings updated their deep-dive guide on building a SaaS sales machine, refreshing a 20+ minute playbook for 2025 that outlines five critical phases for creating a first sales team. The piece details practical...
By SaaStr
Blog•Oct 15, 2025
The Odds of Making It
A new look inside startup growth from zero to $25 million ARR
By Kyle Poyar
Blog•Oct 14, 2025
AI Deals Are Scaling to Massive Valuations. But In Many Cases—Also Massive Dilution. See E.g., OpenAI
So there has never been a “start-up” like OpenAI. Already with 800,000,000+ users and a breathtaking $500 Billion (!) valuation. But it’s also raised and spent epic amounts. So as the chart from FT below shows — all the historic...
By SaaStr
Blog•Oct 14, 2025
If You Ever Think “Should I Fire This Person?” Even Once … Well, Then It’s Time
A new article emphasizes that managers should act decisively when doubts about an employee's performance arise, suggesting that if a leader contemplates firing someone even once, they should proceed with the termination. The piece argues that extending additional chances may...
By SaaStr
Blog•Oct 14, 2025
Everyone Should Be Using Claude Code More
In a recent discussion, Lenny highlighted the transformative potential of Claude Code, an AI tool that operates locally on users' devices, significantly enhancing productivity for non-technical individuals. Unlike cloud-based solutions, Claude Code boasts capabilities such as file organization, image enhancement,...
By Lenny Rachitsky
Blog•Oct 14, 2025
Everyone Should Be Using Claude Code More
How to get started, and 50 ways non-technical people are using Claude Code in their work and life
By Lenny Rachitsky
Blog•Oct 14, 2025
The Data Pendulum Swings to Consolidation
Fivetran and dbt Labs have announced a merger in an all-stock deal, creating a combined entity with an anticipated annual recurring revenue (ARR) nearing $600 million, signaling a strategic shift towards consolidation in the data infrastructure market. This merger reflects...
By Tomasz Tunguz
Blog•Oct 13, 2025
Programming Bottom-Up
Paul Graham's essay "Programming Bottom-Up" introduces an alternative and highly effective approach to software development, contrasting it with the traditional top-down design methodology. While top-...
By Paul Graham
Blog•Oct 13, 2025
Evals, Error Analysis, and Better Prompts: A Systematic Approach to Improving Your AI Products | Hamel Husain (ML Engineer)
Watch now | 🎙️ How to build better AI products through data-driven error analysis, evaluation frameworks, and systematic quality improvement
By Lenny Rachitsky
Blog•Oct 13, 2025
Dear SaaStr: I Want to Keep Doing 1-on-1s With My VPs, But How Do I Streamline Them?
Dear SaaStr: I Want to Keep Doing 1-on-1s With My VPs, But How Do I Streamline Them? 1-on-1s may be partially out of fashion, but most CEOs I work with still do at least some of them. 93% of you...
By SaaStr
Blog•Sep 19, 2024
Dear SaaStr: What’s Your Top Advice For All New B2B Founders?
A veteran SaaS VC advises new B2B founders to temper speed with caution, recommending they pause on uncertain big decisions and extend runway budgets by 6‑12 months beyond original forecasts. He stresses the importance of building a aligned founding team...
By SaaStr
Blog•Jul 24, 2024
Dear SaaStr: How Do You Draw The Line Between Founder and First Employee?
The piece advises that the line between founder and first employee should be drawn by timing and commitment: founders are present before a name, product, code or funds, take essentially all the risk and work for little to no salary....
By SaaStr